Winchester Holiday Deals

Choose two or more items and save on your trip:

Winchester Holiday Package Deals

Airfares, hire cars, hotel bookings and exciting activities — at lastminute.com.au, we can combine all of these things into a neat little package. So, you'll have more free time and more money for Winchester!

With average savings of , you might as well splash a little more on your room (or at least plan an extra night out).

Take a squiz at no less than 400 partner airlines and 282,000 worldwide hotels on our massive database. Then, it's time to craft your unique package deal!

We offer some of the best prices on the market. And that's not all. With our Price Pledge, if you find a lower price on your hotel or package within 24 hours of booking, we'll match it by refunding you the difference.Terms and conditions apply.

Holidays in Winchester

Wondering why Massachusetts is such a massive hit with travellers? Well, we're pretty sure its lovely coastal plains and rolling hills have a thing or two to do with it! Set yourself up in Winchester and you'll be in an excellent spot to get out and experience them.

The nation's capital city, Washington, can be found about 630 kilometres to the southwest of Winchester.

Melrose is overflowing with terrific sights. Just 7 kilometres to the east, here you'll discover the Museum of Science, the Bunker Hill Monument and Old North Church.

Enjoy some time relaxing and reading your favorite book at Herring Cove Beach or Revere Beach.

You'll find some lovely natural sights not too far from Winchester. Why not take off 16 kilometres to Walden Pond? Alternatively, enjoy some of Mother Nature's finest work at Dogtown, 45 kilometres away.

Work on your photography skills at Prospect Hill Park and Royall Park. You're bound to find some interesting subjects to awaken your inner artist!

Love your college football? Then dress in maroon and white and see the UMass Minutemen compete at Gillette Stadium. Located 40 kilometres away in Foxboro, the arena is also the home of the New England Patriots and New England Revolution and often hosts live concerts.

Catch the chairlift at Pats Peak, soak up the blinding white views and then rocket your way back to the lodge. For more snowy thrills, check out what's on offer at Wachusett Mountain Ski Area.

Winter Pond is worthy of a visit. Then, see if you can snap a great holiday pic at Horn Pond.

If you're flying back, it's wise to decide a route to the terminal before leaving. From the centre of Winchester, you'll need to travel some 14 kilometres southeast to Logan International Airport (BOS), the closest airport.

Hotels in Winchester

With a fabulous range of Winchester hotels available, finding the right one shouldn't be hard. At the mo, there are 65 accommodations waiting on lastminute.com.au.

If you'd rather spend cash on adventures than on accommodations, the Harvard Square Hotel and the Days Hotel-Boston/Cambridge are two places you should check out. But then again — you are on holiday. If you'd rather live the good life while you're here, we certainly don't blame you! The friendly staff at the Global Luxury Suites at Kendall East and the Global Luxury Suites at General are specialists in luxury.

Top hotels for your Winchester holiday

citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$335 per night from 13 Apr to 14 Apr
AU$335
includes taxes & fees
13 Apr - 14 Apr
With a stay at citizenM Boston Back Bay in Boston (Fenway–Kenmore), you'll be steps from Newbury Street and 10 minutes by foot from Northeastern University.
"Very pleasant facilities; excellent breakfasts"

Reviewed on 3 Apr. 2025

citizenM Boston Back Bay
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St, Boston, MA
The price is AU$403 per night from 13 Apr to 14 Apr
AU$403
includes taxes & fees
13 Apr - 14 Apr
Harborside Inn Of Boston is in the heart of Boston, within a 5-minute walk of Faneuil Hall Marketplace and Quincy Market.
"The hotel was centrally located and it was a great spot to stay at."

Reviewed on 6 Apr. 2025

Harborside Inn Of Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$345 per night from 8 Apr to 9 Apr
AU$345
includes taxes & fees
8 Apr - 9 Apr
Located in Boston (South End), The Revolution Hotel is within a 10-minute walk of Copley Place and Newbury Street.
"Great discovery! Such a unique and quirky hotel experience with surprising luxury. Wonderful staff!"

Reviewed on 6 Apr. 2025

The Revolution Hotel
Don't see what you're looking for?
See all available properties in Winchester
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

^Savings based on all package bookings made with Flight + Hotel on lastminute.com.au from January 1, 2019 to December 31, 2019, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.